Unveiling the Hidden Side of Org Charts at the NYTimes

0:00Every organizational leader has sat down at some point I think about two things. One, should I reorg? And two, what are the values and principles of my organization? When we do that, we often ask ourselves what we're optimizing for. That's a very reasonable question. What we don't ask is, what do we do with the things that we're repressing? How are we going to reconcile with that? How are we going to acknowledge, I'm putting this to the side? What's the impact of AI-generated code? How can you measure it? Join Linear B and ThoughtWorks Global Head of AI Software Delivery as we explore the metrics that measure the impact Gen.AI has on the software delivery process in its first-of-its-kind workshop.

0:43We'll share new data insights from our Gen.AI Impact Report, case studies into how teams are successfully leveraging Gen.AI, impact measurements, including adoption, benefits, and risk metrics, plus a live demo of how you can measure the impact of your Gen.AI initiative today. Register at LinearB.io slash events and join us January 25th, January 30th, or on demand to start measuring the ROI of your Gen AI initiative today. Welcome back to Devon Routed. I'm your host, Connor Bronsden, and today I'm joined by David Yee, VP of Engineering at this little company called the New York Times. We're going to make it someday.

1:19Yeah, I believe in you. This regional paper is scrappy. The amazing thing about your career, David, is you've scaled both small organizations and frankly enormous ones. in the world of journalism, music, and art. And you have an emphasis on product-oriented engineering and humane management, as I've heard described. And that diverse perspective has led you to identify something that you think is that organizations all have a shadow. Can you define what that means? Yeah. So what's interesting about talking about organizations is we sort of define what they look like. So if you think about the values that an organization has or its org chart.

1:58These are all things that you see. But the thing that I've been obsessed with is this idea that every organization is bigger than that. And the parts that you don't talk about still operate and they are excluded for a reason. So it's those bits that are left on the side that are still operating that show up in ways that kind of like can irritate an organization. And so the things that I've been thinking about is how you bring that together. What are those bits? It depends on the organization. So usually these things are either in conflict with the way you operate. So you could say like, all right, well, we're the kind of organization that makes like really crisp decisions, you know, and everybody owns their decisions, something like that.

2:35But there's always going to be a class of decision where people are like, oh, well, I really need to ask a bunch of people or we need to agree on this. That might not be in your org values. It might not be the way you identify as an organization, but it's still something you need to do. And so if you're going around trying to make sharp decisions about things that need consensus, everyone's going to get just annoyed. And so that's an example. But it shows up in all sorts of different ways. What are the impacts of the shadow? I mean, you mentioned one, but it seems like there would be a variety of ways this would impact different organizations.

3:05Yeah. Generally speaking, the thing it tends to do is like cause dysfunction, slow you down. And it's not that the shadow does that. It's the fact that you have, that you're not sort of engaging with it meaningfully. You're not really acknowledging this is happening. The thing that I was, the example I was giving at lunch was, I was talking to somebody, I was, you know, when you think of an organization, I had this, this debate a couple of years ago with my product partner where I said, we really have to be, we have to make sound technical decisions. And my product partner was like, we need to move fast.

3:38We don't have time to make sound technical decisions. And so like we worked this out, just the two of us, we're working this out, debating back and forth for a long time. Finally, I said, okay, like, you know, we make, we have to move quickly while aiming for sort of technical consistency. now the result of that debate between two people means that there's still this question that the engineers would ask about and this is in a different organization about like where do where do we value show me where we value technical consistency but i do value it's just that when it shows up it tends to fly in the face of the world the org values say that we're supposed to move quickly why would we do this but the answer is you have to do it and so it causes confusion It can cause delay.

4:21It can cause debate. And frankly, for people who find themselves in roles where that, where the shadow, where you're sort of acting on behalf of the shadow, you can actually get really marginalized. And so there's both an organizational process problem as well as sort of, you really have to think about what it means for individual human beings who really aren't acting in service of the publicly stated goals. I think it's interesting because it sounds like this dissonance between kind of the formal structure of the organization and the way the organization actually functions is likely to cause misallocation of resources, both if you want to define human beings as resources, which is controversial at times, but we think of them that way in a lot of ways.

5:02And also, I'm sure how money is spent in the organization, how time is spent. Would that be a good way to characterize this? I mean, it's certainly one aspect of it, right? So if you, I guess I hadn't really thought about it from the perspective of like OKRs or metrics. But it's true that if you say, let's say that you have an organization where the goal is to invent new things rapidly and you're not going to be able to depend on sort of a framework to do that. You're going to have to sort of like hack everything from scratch. And you have another, you have a team that happens to be in your organization that is responsible for sort of a consistent design system or something like that.

5:43If those two things are paired in one organization, you're always going to prioritize the resources for invention. You're never going to prioritize the resources for consistency, even though that consistency is really important. Right? So, but at the end of the day, where do your priorities lie? Where do your values and principles lie? That's where you're going to be paying attention. And you have to ask yourself, at what cost are we not paying attention to this other thing? And like this other thing is just nagging us in the back of our mind. Why are we wasting? Like, and you can ask yourself, why are we wasting so much time inventing new things?

6:15we should be spending time building a design system. So, well, that's not what our org is about. Our org isn't about that. That's something else. So there is a larger question about how organizations intersect and how you really want to sort of bring those, you know, bring that shadow into light is one of the things that I talk a little bit about. Sometimes you bring that shadow into light inside your organization. You can also find the shadow a home in some other organization. I'd love for you to expand on that. That's a really interesting concept. Okay, so first of all, I have to explain that this idea of an organization shadow, and this was sort of part of my talk, it actually emerges from psychoanalysis, and it emerges from Carl Jung.

6:54So I have a whole section of my talk is just about Carl Jung, right? So, and it's a really risky thing to get on stage at an engineering management conference, but I'm going to talk about the Swiss psychoanalyst, but let's just acknowledge the Swiss psychoanalyst, Carl Jung, has this notion of shadow, which is about the psyche and it's about personality, right? So set aside organizations, if I'm the kind of person who says, I'm a confident leader, that's my persona, right? To use also a Jungian term, like my persona is on the, like, and I don't know that I am this, but let's say that I am a strong, confident, convinced leader.

7:30That's how I define myself. That's how I see myself. That's how others see me. That's my conscious self. The unconscious self right behind that contains a shadow, right? So that's where we talk about the shadow. And the shadow contains all the parts that are part of me that don't fit my conception of the person I am. Does it also contain the parts that do fit the conception or do you view it as a separate entity? It's a totally separate entity. So maybe you're not confident in the shadow. Right. Maybe you have doubt. Maybe you're the kind of person who has doubt. The reason it's in the shadow is because doubt doesn't fit my notion of being a confident, convinced, strong leader.

8:07That's not how I want to present to the world. It's not how I want to act in the world. And therefore I push it, push it down. I push it down. I repress it. But eventually it'll come to the forefront. It's there, right? Like, and you know, any confident leader, like some, if you invert that any leader who is devoted to consensus may have a gut instinct, that gut instinct may be in the shadow and it emerges. You don't really know what to do with it. And so there's nothing wrong with doubt. Doubt's not bad. It's, it is a tool, right? Right. And so ultimately, this kind of gets the point. It's like the goal, one of the way I close the talk is basically talking about integrating the shadow.

8:46And both in, you know, psychoanalytic terms, but also in organizational terms, what you really want to do is bring that to light and say, listen, sometimes as a leader, I kind of doubt myself. it serves me in the following ways and it actually helps make sure that I'm making more more informed decisions in moments that are not certain. Maybe I understand the risks whereas if I was fully confident I would ignore the risks. Right exactly and that's what happens to a lot of people so if we take that hypothetical leader that person's going to run you off a cliff if they ignore that shadow so it's really important to integrate the shadow the same is true of organizations so if you take that same model and I don't know that necessarily this is the best example, but let's, let's follow it.

9:31That you've got sort of design consistency in your shadow. Okay. Right. I have to make consistent design. Like it makes my product easier to use, but that gets in the way of, of innovation gets in the way of your public persona of innovation. You have to ask yourself, how am I going to invite this consistency into the work? How do I acknowledge, listen, nonetheless, this is something that my organization needs to do? How do I bring it in? In a complex organization, the answer might be platform thinking. And you want to move that into a platform space, someplace that's going to be able to have the leverage.

10:05It's going to be able to provide the leverage. So this is maybe building a platform team or something. Exactly. Exactly. Right. And you bring that to light and you say, look, we need a platform team. Even though our job is to innovate, we need a platform team because ultimately it's going to help us move faster. And so I think that's one way of thinking about the reintegration of an organization's shadow. This is fascinating because you've also just given me a great argument for why people need platform teams. Yeah. Yeah, enable innovation in your organization by getting rid of your organizational shadow and orient it to the platform team so they can solve your problems.

10:36I love it. And it broadly sounds like you think engineering orgs need to think more in depth about organizational design and the psyche of that organizational design. Every organizational leader has sat down at some point to think about two things. One, should I reorg? And two, what are the values and principles of my organization? We do that as an organizational tick. We do that as leaders. And of course, those things are necessary. When we do that, we often ask ourselves what we're optimizing for. That's a very reasonable question. What we don't ask is, what do we do with the things that we're repressing?

11:13About like, how are we going to reconcile with that? How are we going to acknowledge, like, I'm putting this to the side? Or sometimes down the line, how do you find yourself in a situation where something is happening and you're confused or annoyed and you're saying like, but I thought our value was this. How do you look at that moment of decision when you reorged, when you sort of wrote your values and principles and said, oh yeah, I made a conscious decision not to include that in the values. Nonetheless, it is important right now. Like, your organization still needs those things. If it didn't need those things, they wouldn't be coming out.

11:47And I'm not saying you have to write like a 33 point org values document, but sometimes you need to ask yourself, how do I invite these tensions into conscious view so that I can reconcile them? Interesting. So because they're out of view, they continue to cause extra problems, almost like having like, I don't know, like a burr in your clothing that you can't get ahold of. And once it's out, you can get rid of it. You can deal with it. you can leverage in whatever way you want to. And so you're looking to say, how can I leverage these challenges in a way that's positive for the organization? Because we know we actually do need to solve them or use them or else we're going to invite more risk.

12:29Yeah, we're going to invite more risk. And frankly, we're going to waste a lot of time and energy. And frustrate people. Yeah. This is in, I mean, I'm not the kind of person who says, well, if you use this one simple trick to fix your organization, but I do. We're going to title a podcast. Sorry. This one simple trick. I think that the, when I think about operational efficiency, and this is just my, this is the way that I think. Think about operational efficiency. I'm not thinking like, okay, if we could just use AI for this, or if we could just have engineers work longer or harder, we could get more done.

13:01A lot of times when I look at the things that slow us down, it's related to confusion, disagreement, and delay. and that delay often emerges from a sense of uncertainty that says I usually know what to do but in this moment I don't know what to do and I'm really afraid of making a decision because I'm afraid I'm going to be held accountable for doing something contrary to the values of my organization or I'm going to be acting out of turn or like I don't know I feel like I should ask the VPE about this when actually sort of acknowledging no sometimes like there are decisions that need to get made in ways that don't mirror the values or don't mirror the hierarchy of your org Right.

13:40And then that creates additional communication costs by that confusion. Because now suddenly you're talking to the VP, you're spending their time, you're spending your time, you're diving into this problem that hopefully if the shadow is better integrated into your organizational structure, you'd be able to solve because you understand how to think about this prioritization, how to think about this context. Yeah, because at that point you would have said, you will have said. And it's really funny actually because recently we had this conversation in my part of the organization where rather than sort of stating the values, we actually stated the tensions.

14:07intentions so so one of those tensions i'm trying to think of like a really good one of those tensions was sort of i need on one hand you say i need the liberty to act independently and on the other side you say i'm afraid of stepping on people's toes and both those things are in play right if i look at the organizational values of the new york times one of them is independence right so the former is really independence i'm going to act independently and I'm going to like depend on my research and I'm going to make a thorough point of view and I'm going to arrive at a decision. But you'd be surprised how much in my organization there's a fear of stepping on people's toes.

14:47Now, don't step on people's toes is not written in the organizational values of my business. But it's there and you have to be able to talk about it. And so I, like one of the ways we did that recently was bringing those up as tensions and saying, how do you want to reconcile these tensions? That's the work of integration. You have to say it out loud. Do you think that's the result, this specific tension of not wanting to step on others' toes, of a way that the New York Times culture functions, or is it a result of people's previous experiences that they're bringing to the table? I tend to think it's all the manifestation of past experiences.

15:20I don't think, for example, I don't think that the New York Times would say that in any way. I don't think it's representative of like what the New York Times would be about. There's no reason to make that sort of part of the values. I think that there's historically, in any organization, there are past experiences that organization has had or that individual people have brought to that organization that have caused pain. And as a result, you repress that. You say, I'm not going to do that again. And it could be, one of the things I think a lot about is it could be that the, that the people involved in those events and those decisions and the way they unfolded, they're gone or those conditions are no longer true, but you have, you've made a decision.

15:59You carry that cultural baseline or foundation that was created by folks at an organization. I mean, frankly, we do as a society, right? Like we're still building off of the culture that was here beforehand. That's, that's absolutely right. And like frequently those things, because, because you, if, when you look squarely at them, you, like I said, you wouldn't say like, yeah, I'm going to go ahead and put this one in the constitution. Like it's there that operates. And so you have to be able to ask, well, what am I going to do about this? And you have to be able to acknowledge that it's happening because if you don't acknowledge that it's happening, you can't solve for it.

16:33what prompted you to apply this concept of the shadow from Carl Jung to org design? What, what inspired this? So originally when I was thinking about this, so, you know, Lee Dev said, Oh, Hey, come get this talk about influence at scale. And I said, okay, how am I going to do the influence at scale? I said, well, I could talk about like communication practices. I could talk about tailoring a message. I had all these ideas. And then I said, why is it that our org charts don't work why is it that a manager can't make a decision in their scope or the vp of engineering can't act um without getting full buy-in from the product partner of a of another vice president of engineering someplace else in new work there's something happening right and um it just so happened at the same time i was taking i was part of this coaching program that thinks about Jung a lot, that was talking about Jung a lot.

17:29And so it was surprising, like as you dive into shadow work and Jung's concepts of shadow, it's really hard to internalize what that is. And so as I was, I was thinking about these two things at the same time. And so I was telling my friend Neha, who's presenting also today, I was like, I think of these things as shadows. There's a book that I cite in my talk about sort of managing the organization shadow or mapping an organization shadow. And it's, and it, I discovered it and it's sort of to connects these two bits. It connects union psychology with organizational thinking. Uh, and so actually that leaping off of that helped me sort of formulate the connection between these two things that were going into my head.

18:07I would be curious if you could share an example of an organization that is either doing a great job integrating its shadow or maybe a terrible job. I mean, honestly, my assumption is that all organizations are doing a terrible job of this, right? If they weren't doing a terrible job of this, then, you know, then we wouldn't have any, we wouldn't have our work, right? Like this is the reason why I'm giving this talk here today is because as senior leaders, as sort of directors and vice presidents of engineering, there's a bunch of unsolvable problems that sort of bubble up to you, right? An engineering manager is having a problem with another engineering manager or this process that you set up isn't working.

18:44And so the natural process organization is to pump this up and you go this up to the next, up to the next level. So you're talking about directors, VPs of engineering, other kind of senior leaders. So by definition, our job is to solve problems that are designed systems are not equipped to solve, which means that like you have to look at the, you have to look at the problem and say, okay, well, what's, what's at play here? All of us do a really bad job of this because we've, we've worked really hard to create working systems, healthy systems to be able to serve these needs. You know, I can, you can imagine sort of any number of organizations that, that are well known for sort of healthy, healthy cultures.

19:29So Netflix, for example, when I don't work at Netflix, so I can't speak for Netflix, but legendarily from the outside, everyone says, well, you know, Netflix has this figured out. They have this culture document. It defines everything. If you follow the culture document. It's just going to work. It didn't work for them as they scale. Everything that they've done in the last year of their existence has been to sort of question their culture document. So in a sense, you might say, okay, Netflix is looking at the shadow and saying like, this isn't working. And you could talk to anybody at any high functioning organization and say, oh, it looks like a great organization to work at.

20:01And they say, yeah, well, on the ground, it's a little more complicated. Right. Right. That's real. So if it's more complicated, What do you do with that? You could imagine that an organization like Netflix, in making the decision to sort of like question their culture document and change their processes, is trying to integrate the shadow. Whether they're doing a good job or not, I don't know. But that's just one example. Again, I think most organizations of any complexity, and probably the more complex or the more tenured the organization, the harder time they have of doing this, find difficulty in reconciling the shadow by design.

20:34This is really interesting. I love to use Netflix as an example because I spoke with Carol Barrett at Netflix about their transition as they've started to hire more junior engineers and some of these changes they've made. And what you're saying resonates. Netflix, we're speaking for them. We don't work at Netflix. But I think by your definition has been wrestling with that shadow where maybe that shadow, and again, I'm just guessing it grew over the years. But I said, this doesn't now work for us as well as it used to. we've added these cultural pieces that maybe we haven't fully accepted or that we need to adjust to and now they're saying okay how can we integrate parts of that shadow to improve the organizational and I would be curious if they think that's what they're doing and that's how they're improving the organization or how they would think about it and maybe an interesting follow-up for Carol or Catherine here today is asking them like what do you think that would Netflix have been doing integrating the shadow does David's talk resonate?

21:28Yeah, I will ask so did I did I really change your mind? And like, are you convinced now that I was right about the way Netflix ought to work? Let's get someone from Netflix. Come on, like the producers, can we grab someone? Yeah. Give me a call. They're shaking my head here. Yeah. Maybe they'll call David after this. Yeah. I'd love to add some more context to this. So let's talk a bit about what you do at the New York Times and your organization there. Because I think that'll be a great corollary to this. You know, the shadow side of the organization versus the tensions versus how your organization functions.

21:58How big's your org at the New York Times? So my organization in the New York Times, I have nine direct reports. I have about 70 engineers all told. And it's an organization called Subscriber Experiences. Think of this as the organization that is responsible for the homepage of the New York Times, the newsreader application. If you like read the New York Times on your phone, like that app, that is an app that we own. It's in conjunction with a lot of other teams. Things like personalization of the experience and the emails you receive, right? All of these are like sort of how do you bring the product to subscribers?

22:32So when you describe me as a product-oriented engineering leader, that's my bread and butter. That's the kind of organization that I'm in. So that's kind of my zone. And, you know, it is a discrete mission. We have a mission system. So it's a discrete mission inside the New York Times, inside an organization called XFUN. And so we have our own practices. We have our own principles. We have our own values that supplement those of the New York Times. We don't operate exactly like the organizations around us. And yeah, like we have, like you said, we have our own tensions, our own problems that are unique.

23:06And like, we also reflect on the problems and tensions of the organization as a whole in our work. You have to. Would you be open to sharing some about how your org works and then some of the tensions you identified? I know you mentioned one earlier. Yeah. So this is always like the classic engineering debate is like, do I move fast and break things or do I make the right decisions up front? Right. So that's, that's how, which is hard to do. That's hard. As it turns out, um, you can't really live by one or the other without, you know, you have to like, you have to eat your hat eventually. And so one of the things we're figuring out now is, okay, how do we, how can we bring products to market really, really quickly while pointing?

23:41And so this is, so if you let's, if the process of reconciliation looks a little bit like this, if we were writing an, an org value for subscriber experiences, we might say we We need to bring products to market as quickly as possible to evaluate whether they serve our readers and serve our newsroom in the right way. Right. And then we would leave everything else on the floor. But by bringing up his attention, we can say we're going to build things as quickly as possible to bring them to market and experiment. But as we do it, we're going to identify the journey we're going to take to a consistent, scalable, resilient, extensible user experience.

24:15Right. So we're still going to be optimizing for one thing, but we're going to be doing it in tension with this thing that would otherwise live in our shadow, which is making sound technical decisions as we work. We are going to do this today, but in six months, we're going to be lining up this batch of work that brings it along. That's not like an uncommon gesture in engineering, but one of the things I appreciate about the way we've been thinking about this is that you can say it up front and you can say this is it's not this, but that it's more like this in light of the long term, the short term in light of the long term.